22620

Quinine

suitable for fluorescence, anhydrous, ≥98.0% (dried material, NT)

• Synonym(s): 6′-Methoxycinchonidine
• Empirical Formula (Hill Notation): C₂₀H₂₄N₂O₂
• CAS Number: 130-95-0
• Molecular Weight: 324.42
• Beilstein: 91867
• EC Number: 205-003-2
• MDL number: MFCD00198096
• UNSPSC Code: 12171500
• PubChem Substance ID: 57647993
• NACRES: NA.32

Properties

• Assay: ≥98.0% (dried material, NT)
• form: powder
• optical activity: [α]20/D −126±5°, c = 1% in chloroform
• impurities: ≤5% dihydroquinine (HPLC)
• loss: ≤1% loss on drying, 110 °C
• mp: 173-175 °C (lit.)
• solubility: H₂O: soluble
• fluorescence: λ_ex 347 nm; λ_em 448 nm in 0.5 M sulfuric acid
• suitability: suitable for fluorescence
• SMILES string: COc1ccc2nccc([C@@H](O)[C@@H]3C[C@@H]4CCN3C[C@@H]4C=C)c2c1
• InChI: 1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19-,20+/m0/s1
• InChI key: LOUPRKONTZGTKE-WZBLMQSHSA-N
• Gene Information: human ... ABCB1(5243) , CYP2C9(1559) , CYP2D6(1565) ; rat ... Cyp2d1(266684) , Cyp2d2(25053) , Cyp2d3(24303) , Cyp2d4v1(171522)

Description

General description

Quinine, also known as 6′-Methoxycinchonidine is a fluorescent reagent. The quantum yield of Quinine is 23% higher at 390 mµ excitation wavelength than at 313 mµ. The fluorescence polarization in the emission band of quinine in a rigid medium arises from two singlet states simultaneously. The emission spectra of quinine or 6-methoxyquinoline shifts towards the red zone when excited at 390 mµ.

Application

Quinine was used in the following processes:

• To study its in vitro antimalarial activity in combination with omeprazole.
• To analyze its effect on viscosity and friction of saliva.
• As a test agent to study its impact on the accumulation of the fluorescent P-glycoprotein (Pgp) substrates in P-glycoprotein overexpressing breast cancer cells.
• To study its influence on the pyramidal cell intrinsic properties, extracellular potassium transients, and epileptiform activity in vitro.
• As a reference compound to identify alkaloids by phytochemical screening of Deianira erubescens, Strychnos pseudoquina and Remijia ferruginea plants.

Biochem/physiol Actions

Potassium channel blocker

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302,H317
• Precautionary Statements: P261 - P264 - P272 - P280 - P301 + P312 - P302 + P352
• Hazard Classifications: Acute Tox. 4 Oral - Skin Sens. 1
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 1
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves